This Time Around
by donna79
Summary: You never forget your first love. They stay with you long after you have moved on. What if you were given a chance to do things right? Set a few months after the finale.
1. Deja Vu

**Story Title: This Time Around**

**Summary: You never forget your first love. They stay with you long after you have moved on. What if you were given a chance to do things right? Set a few months after the finale.**

**Pairing: Rory/Dean**

**Disclaimer: I do not own Gilmore Girls. It belongs to Daniel and Amy Sherman Paladino. What I do own is the concept for this story, so please don't use it without my permission.**

**AN: Just a quick note: I am basing Dean's look on the way he looks now because my dad and I are semi-obsessed with the show Supernatural. I've watched it from the begining and Jared Padalecki's hair gets longer and more Fabio-like with every season. lol And do you want to know something else that's funny? I'm a Dean girl when it comes to that show too. Ay yi yi**

After a long summer and fall spent following who was now the President of the United States Rory had made her way back home. Not necessarily to her mom's but to Stars Hollow. She had missed it more than she had thought was possible. It hadn't taken her long to find a house for rent. She'd mentioned to Miss Patty that she was looking for a place and by the end of the day Miss Patty had found her five places to look at. The woman really did have her finger on the pulse of the town, nothing got by her.

She lived close enough to her mom that Lorelai would pass her house every morning on her way to work. She lived across the street from Lane and Zack which made things even better. She was starting to adjust to things when one fateful trip to Doosey's changed her life for the better.

She was grabbing a few things that she'd forgotten when she came in earlier in the day. The only reason she was making Thanksgiving dinner was so that Luke didn't have to. She was trying to decide between mini or jumbo marshmallows when someone's arm reached past her from behind. The person apologized and her breath caught in her throat. Her head swivled slowly to look over her right shoulder.

His hair was so long that it covered his ears and fell in his eyes but she would know those dark eyes anywhere. She had thought that she would never see him again. The last she'd heard he had moved back to Chicago.

"Hi," he said shakily.

"Hey," she said, the air being sucked out of her again.

"I should probably move, maybe then you won't look like a frightened baby deer," he said with a sigh.

"I'm sorry," she said quickly.

"It's okay. Stars Hollow is pretty small; we were bound to run into each other eventually," he said, shoving his hair out of his face.

"Dean?" A young girl called from the end of the aisle.

Clara had to be at least nineteen now. She had grown up to be really beautiful with her shoulder length blond hair and long legs. She wasn't as tall as Dean but she almost was. Dean started to walk away but Rory put a hand on his arm. He looked down at her hand before meeting her eyes.

"We're both adults. There's no rule that says that we can't be friends," she said reaching into her purse for a pen and a piece of paper.

She found a post-it pad embossed with Hello Kitty and a red glitter gel pen. Her mom had purse bombed her again. She sighed mutedly as she scribbled her number onto a post-it then tore it off the stack. Dean shook his head with a laugh. He took the pad and pen from her and quickly jotted his number down.

"I'll only give this to you if you promise to call me," he said.

"I promise," she said with a nod.

"See you around Rory," he said with an easy smile.

That smile had threatened to melt her heart as a teenager. Her heart skipped a beat as she watched him walk away. She grabbed a bag of mini and a a bag of jumbo marshmallows without looking. She would be on the safe side and she'd have something to snack on; it was a win/win.

XXXX

Rory had shown up at the Inn half an hour early so that she would avoid her mom. She had promised her mom that she would help decorate the bedrooms for the holidays since three of the maids were on maternity leave. She was draping holly over a gas fire place mantel when someone knocked on the door. A few seconds later Lorelai stepped in.

"Hey," Rory said over her shoulder.

"Hey. I thought that we could get something to eat before you started."

"I didn't realize that you wanted to," she said apologetically.

"It's my fault. I should have mentioned it. Sookie's talking about trashing a ginger bread house because the gumdrops are clashing with the frosting design. How about we save it?" Lorelai asked hopefully.

"Sure," Rory said, going back to what she was doing.

"Come and see me before you leave?"

"Okay."

Lorelai left the room, closing the door quietly behind her. Something was off, she could sense it. Alarms went off in her head when Rory not only wouldn't meet her eyes but she didn't stop what she was doing. A busy Rory was a Rory who had something to hide.

Rory made her way downstairs an hour and a half later. She went into the kitchen to find Sookie in the middle of yet another crisis. Sookie had cut her arm just above her elbow. One of the servers got her to sit down before wrapping a towel around Sookie's arm. She was definately going to need stitches.

"Hey Peaches, I packed up your half of the house, it's on the counter," Sookie called over the noise.

"Thanks. Can you tell my mom that I'm taking off. I've got plans with Lane tonight."

"Sure thing, have fun."

Rory grabbed the container and booked it down the hall, past the check in desk and out the door in less than a minute and a half. If her mom had seen her than she hadn't tried to stop her. She slumped against her seat trying to slow down her racing heart. She didn't like keeping things from her mom but she kew her mom would have something against her talking to Dean. She was an adult and she didn't have to tell her mom everything.

XXXX

Lorelai put her feelings about Rory aside after she left work. She had an appointment with a flower vender that Sookie had recommended. She had hoped that Rory would come with her but she understood that Rory had a life of her own. Rory had gone with her to every dress fitting. She had decided to use the dress that she had found when she and Luke were first engaged. The dress couldn't be more perfect even if she would be wearing a white wool coat over it. Nothing would stop her from getting married in the gazebo.

She wanted simple flowers, maybe Christmas hostas or white orchids with red poinsettias along the aisle since they would be getting married on New Years Eve. Luke had taken her by surprise by giving her her engagment ring back and announcing that he still wanted to get married.

Her life hadn't been the same when they weren't together. She had been lying to herself when she thought that Christopher would ever take to living in a small town. Her whole life was there and she couldn't uproot it.

She had put her hurt feelings about being lied to about April aside. After thinking about it, she realized where Luke was coming from. Learning that you had a daughter who was kept from you for twelve years is a big shock. Lorelai liked April, she was a good kid who was luckily was nothing like her dad. She'd had a partner in crime when she decided to gang up on Luke when Rory wasn't there. Honestly, April reminded her of a more chatty version of Rory.

Luke had moved in with her and turned the room over the diner into an office. He was still getting used to the change and Lorelai was patient with him. It was hard breaking certain habits that you'd had for most of your adult life. Things were getting better every day.

Lorelai wasn't used to Rory keeping secrets. If Rory was keeping something from her it was more than likely something that she wouldn't approve of or it was about a guy. She just prayed that it wasn't both because with Rory that was usually the case.

XXXX

Rory was going over an article that she would be sending to the New Yorker when her phone rang. She picked her phone up to see Dean's name staring back at her. She pressed the answer button and saved her work at the same time. It wasn't due for a couple of days anyway.

"Hello?"

"Hey."

"Hey yourself," she said with a smile.

"You're up late."

"So are you," she countered.

"I was going over some blue prints."

"Are you working with Tom again?"

"Sometimes. I design houses," he admitted.

"Wow, that's great," she said in surprise.

"Yeah, my parents are really proud. The four years of architectual school they helped pay for are paying off," he said with a light laugh.

"You decided that college was for you after all?"

"Yeah. I realized that I had an eye for architecture not long after we stopped seeing each other last. My parents talked me into moving back to Chicago for school and I moved back a couple of months ago," he explained.

"I'm really proud of you."

"Thanks. I'd ask what you've been up to but everybody here seems to know. Babette told me you were on the campaign trail with Obama."

"Yeah. It was surreal. I found myself doubting if it was really happening half the time."

"I thought you wanted to be the next Diane Sawyer."

"Even Diane Sawyer had to start somwhere."

They talked for a few minutes longer before he had to get off the phone. She was glad that he'd called. She had been thinking about him a lot since she had run into him the day before. The feelings that she had for him were slowly coming back without her realizing it. She was reluctant to start a relationship with him since they had both played a role in the demise of their relationship. They were going to have to set some boundaries and guidelines if they were to start dating again.

XXXX

It had been three days since Rory had seen her mom. Avoiding her had been easy since her mom was a creature of habit and rarely varied from her morning routine. Rory had taken to working late and sleeping in, giving her mom plenty of time to leave Luke's and be at work before heading out. She couldn't keep this up forever, her mom was bound to grow tired of being ignored eventually.

Her luck finally ran out that weekend. Her mom had shown up at her house with breakfast and Rory knew that it was time to tell her the truth. They ate in the kitchen since the couch and coffee table were overflowing with her work.

"You've met someone, haven't you?" Lorealie asked.

"I ran into someone, Dean," Rory admitted with a nod.

"I've seen him around town but I thought that he wasn't staying," Lorelai admitted.

"He's back to stay. He went away for college and now he's starting his own business. He's really matured since you saw him last."

"He's also in dire need of a haircut, he's starting to look like the Shaggy Dog."

"I was thinking Jesus, but you always have to take it one step farther," Rory said with a shy smile.

"So, what does he do?"

"He's an architect, he designs houses."

"Are you two..."

"We're just talking right now. Thanks for the post-it's and pen by the way."

Lorelai grinned evily befor taking a sip of coffee. She had trouble trusting Rory's judgment when it came to guys since Jess. Even Dean had failed her when he had cheated on his now ex-wife with Rory. She had been worried about her after everything that had happened with Logan. She hoped that Rory would be smarter this time around.

**AN2: Sorry this is so short but this is a new couple for me to write even though Dean was my favorite of all of Rory's boyfriends. I hope I got at least one person's attention. Let me know what you guys think.**


	2. Hitchin' A Ride on the Crazy Train

**Disclaimer: I do not own Gilmore Girls.**

**AN: I want to say a couple of things before you all start reading. First and for most thank you to all of you who have reviewed, favorited, and are following this story. I really apreciate it. Secondly I am so sorry that this chapter took so long to get out. I couldn't remember any of the babies names on the show and I didn't want to update this chapter without mentioning Liz, TJ and their daughter. Thanks for baring with me.**

What had she been thinking when she offered to cook Thanksgiving dinner for nine people, ten if you included her. She must had been insane when she refused Luke's help. She had learn how to cook a few things while in college but not enough to pass for a holiday dinner. She'd bought a few cookbooks and had spent hours pouring through them to find just the recipies she wanted. Luke and his side of the family would be happy with anything but her mom and grandparents took Thanksgiving seriously and she didn't want to let them down.

It had taken a lot of coaxing to talk Richard and Emily into canceling their annual Thanksgiving dinner and coming to Stars Hollow but Rory had done it. It was now the night before Thanksgiving and she was going over her list of things that she needed to do. She knew that her grandparents were expecting a culinary fantasy but what they were going to get was store bought pies and stuffing from a bag. They were in for a rude awakening.

She had handed the turkey cooking duties to Luke since it was the focal point of the meal and she didn't want to mess it up. He was even taking half the day off so that they wouldn't have to eat at the diner. She couldn't wait to impress everyone with her cooking skills.

She had decided against inviting their friends in favor of keeping the event small and give her grandparents a chance to meet April, Liz, TJ and Doula. She didn't find out until a few days that Jess was coming in for the day. She hoped that her grandmother wouldn't bring up what had happened the last time she had seen Jess and would at least try to be nice to him.

She had only talked to Dean twice since telling her mom the truth. He had been in and out of town for meetings and she was starting to realize how serious he was about his work. Most of his business was based out of New York and he was starting a second office in Hartford. Rory admired his work ethic.

It was only a matter of time before Dean took over her thoughts. She hadn't wanted to fall back into the routine from five years ago. Neither of them were the same people that they had been the last time they saw each other. They were more mature and better equiped to handle the bumps in the road that life always seemed to throw at them.

She had thought of inviting him but before she could he told her that he was going to be going to Chicago for Thanksgiving since his grandfather wasn't doing well and his family wanted to have one last holiday with him. Luke had called her less than an hour later to let her know that Jess would be coming so it had worked out for the better. Even though they were both older and wiser; Rory hadn't wanted to take the chance of having to referee a wrestling match while trying to get dinner on the table.

Rory woke early the morning of Thanksgiving to hear someone moving quickly through the house. She sprung from bed, grabbing her bathrobe as an afterthought and throwing it on as she jerked open her door. She found Sookie in the kitchen pulling a pie out of the oven.

"Do you have any idea what time it is?" Rory asked, her voice panicked.

"It's just after six," Sookie said over her shoulder.

She placed the pie on the counter where three other pies and a very large turkey sat.

"Did your stove break on you or something?"

"No, why?"

"Than what is with the food, Sook?"

"This is for you guys," she said with a shake of her head.

"I was planning to get up in less than an hour to start dinner; plus Luke is cooking the turkey," Rory explained in a tired voice.

"Fine, I'm glad that you stopped me from throwing the bird in. I'll just leave everything else and get out of your hair," Sookie said in a defeated voice.

"Take the pies too," Rory added.

"You mean these pies?" Sookie said holding one up for Rory to see.

It was Sookie's famous caramel pie; one of Rory's favorites. Sookie quirked an eyebrow with a knowing smile. Rory sighed in defeat, throwing her hands in the air.

"I remember your mom saying that your granddad liked bourbon pecan pie but I haven't had a chance to put it in the oven yet."

"What am I supposed to do with the pies in my freezer?"

"You can make them for yourself."

"Do you honestly think that I can put away five pies on my own?"

"Not at one time," Sookie reasoned.

"Get the pecan pie in the oven and then you're leaving," Rory said before turning on her heel to head back down the hall to the bathroom.

She heard Sookie leave as the shower started and after she had dressed for the day she made her way back into the kitchen where the smell of pecans filled the house. There was a post-it on the fan over the stove letting her know to take the pie out at a certain time. She was pulling the pie out five minutes later when the front door opened. Lorelai stuck her head in, sucking in a long breath. She sighed in contentment when the smell of caramel, pumpkin and pecans mixed together hit her nose. She knew giving Sookie the okay to make the pies was a good idea.

Jimmy Buffett schooling everyone on how to say Merry Christmas in Hawaiian from the living room was welcome background noise. She had come three hours early as a peace offering when Sookie called her to let her know that the jig was up and Rory had banned her from the house. Lorelai stood at the entrance to the kitchen watching Rory page through a recipe book.

"I know that you sent her over here," Rory said without turning around.

"How did you know that it was me?" Lorelai argued.

"The smell of your traitorous ways gives you away," Rory accused.

"Mommy's sorry," Lorelai said in a apologetic child's voice.

"Save it Benedict Arnold. Luckily I stopped her after the pies were made but before she dressed the turkey."

"That is the best time to catch her in the act. Do you need me to do anything?"

"Yes, stay far away from the stove," she countered.

"Mean," Lorelai pouted.

Lorelai looked through the paper deciding which black Friday deals she wanted to go to and which ones were just not worth the effort of staying up all night and well into the tomorrow afternoon for. She and Sookie had gone black Friday shopping every year for the last decade. By the time they got home they were so haggard and tired that Lorelai wouldn't talk for the rest of the day. Rory liked cyber Monday better and she didn't have to leave the house, she had tried to get her mom to see that it was easier but there was no arguing with Lorelai when she had made up her mind about something.

XXXX

Lorelai was having trouble keeping Luke out of the kitchen. He was almost as bad as Sookie but instead of wanting to control everything all he wanted to do was help. TJ had been able to talk him into watching a football game with him but it barely held his attention. Baseball was Luke's thing; he hadn't watched a football game in over a decade but he appreciated TJ's effort to help.

Richard and Emily had arrived the same time Luke had and the best thing he could say about their awkward talk in the yard was that at least they had been cordial. The Gilmore's had made it clear that he and Jess were outsiders and that they were going to have to prove themselves before their trust would be earned. Jess had almost bolted when Emily opened the door for him a little while ago. Richard had been polite to him when Lorelai introduced them but Luke could tell that Emily had filled Richard in on what had happened the last time she'd seen Jess.

Lorelai came into the kitchen as Rory was pulling the stuffing out of the oven.

"How's it going in here?"

"I'm almost done. Can I trust you to set the table or do I need to ask someone else to do it?"

"I can do it," Lorelai said with a nod.

"You won't fold the napkins to look some kind of animal doing something dirty?"

"I did that one time! You thought that it was funny if I remember correctly," Lorelai said, her arms folded over her chest and her head bobbing to enforce her attitude.

"Yes it was, but Grandma, Grandpa, and Luke won't think that it is."

Lorelai knew that she was right so she stayed silent. She carried the plates, silverware, and cloth napkins that Emily had let Rory borrow into the dining room first. Rory was pulling the yams out of the oven and turning off the stove when she came back in for the glasses. She set the table in silence, feeling her mother's skeptical eye following her around the table. She was waiting for her mother to say something about the way she was setting the table but she never did.

Rory started to bring the food in and Luke was able to sneak into the kitchen to grab something to bring out. She nearly collided with him when he came through the revolving door closing the kitchen off from the living room. He gave her an apologetic look and she just shook her head with a small smile. They worked together to get the rest of the food onto the table while it was still hot.

Once everyone was sitting down TJ mentioned that his family took turns going around the table and each person would say something that they were thankful for.

"The rest of you don't, but would it be alright if I did?" he asked Rory.

"Sure," she said with a encouraging smile.

"I'm thankful to have the chance to meet not only Jess for the first time but to meet Richard and Emily."

"That's really nice Teej," Liz said with a nod.

"My family did that too," Emily did that with a sad smile.

"I didn't know that, mom," Lorelai said as she poured herself a glass of wine.

"Your father wasn't raised the same way I was so I never brought it up," she said politely.

"How about we restart the tradition today?" Richard broached.

Emily looked at Richard with a pleased smile before standing.

"I'm thankful that our granddaughter thought to put this together and then brought us all here together."

"Here, here," Lorelai said.

"Jess, you're next," Liz said.

"I'm thankful that my mom finally stopped calling me Jesse," he said before sitting back down.

"It's your name," Liz argued.

"I've never liked it," Jess said with a shake of his head.

"I'm thankful to not have to work today," Luke said to take the focus off of Jess.

"Amen," Liz said with a laugh.

"Do you usually work on Thanksgiving, Luke?" Richard asked.

"This is the first one I haven't since I opened the diner."

"He rarely takes a day off at all," Lorelai informed her dad.

"That sounds like someone else I know," Emily said giving Richard a knowing look.

"Mom?" Rory prodded.

"I'm thankful to be spending Thanksgiving with all of you," she said with a smile.

Rory stood next, not knowing what to say. She mulled over what to say as she took a sip of wine.

"I'm thankful for second chances."

"That's a little vague," Liz said with a dry laugh.

"Just second chances in general," Rory said with a shrug.

A second chance for Luke and Jess to meet her grandparents and also another chance with Dean even though this was technically their fourth chance, but who was counting? Lorelai nodded in agreement, thinking of her own second chance with Luke.

"I'm thankful not to be pregnant this year," Liz said with a sigh.

Liz had been so miserable while she was pregnant with Doula at the end of last year she hadn't even celebrated Thanksgiving and had to be corced into spending Christmas with TJ's parents. Doula garbled and cooed from her high chair and Liz smiled at her sentimentally.

"I'm thankful for my health," Richard said with a slow nod.

Emily, Lorelai, and Rory agreed. It had been touch and go for a while but Richard had finally agreed to slow down. He worked from home most days and only went into the office one or two days a week, he had even stopped working on the weekends, something that he had done for more than thirty years. It was a miracle that he was still alive.

The conversation was lively and Liz had no problems carrying conversations with not only Richard and Emily but Jess at the same time. Jess was making an effort to be polite and Emily's attitude towards defrosted as the day drew on. Richard was able to talk the three men into having a cigar on the front porch while Lorelai and Liz cleaned up after dinner. Rory and Emily sat on the couch facing each other catching up on each other's lives.

"So is there anything new with you?" Emily broached.

"Not really. I'm working like a madman most of the time."

"No significant other?" she proded.

"No," Rory said with a thoughtful look.

"Your mother warned me that Dean might be here. Why wasn't he?"

"His grandfather isn't doing well and this might be his last Thanksgiving so his family went to Chicago. Did my mom tell you that we were dating?"

"No, she just said that the two of you were talking. Do you think that the two of you might get back together?"

"It's too soon to tell, we're still getting to know each other again."

"Bring him by the house when you have a chance, your mother said that we might have been a little too hasty to judge him when the two of you were younger."

"Yes ma'am."

Rory was glad that her grandmother was open to the idea of seeing Dean and was touched that she had thought to extend the invitation for him to come over. She didn't see it happening for a while but she was grateful for the offer.

"Rory?" Jess asked from the archway to the living room.

"Go, we can talk later," Emily encouraged her.

Jess and Rory stood on the porch after her granddad, Luke and TJ had gone inside. They didn't say anything for a while, comfortable with the silence.

"Are you going back to Philidelphia?"

"Yeah. I've got a deadline to meet. What did you mean when you said that you were thankful for second chances?"

"Just in general. I mean, it's an act of fate that you showed today and my grandmother didn't throw you even one icy glare," she reasoned.

"Did I hear you tell her that you're talking to Dean again?"

"I am. I ran into him a couple of weeks ago and we've talked a handful of times."

"Is he still mad at me?"

"I don't think so. We haven't talked about you that much."

"I just wanted to thank you for letting me come today."

"It's not a big deal, the rest of your family was here so I wasn't going to tell you that you couldn't come."

"I would have understood if you had."

"I don't want you to feel like you can't come and see your family. Are you still coming to wedding?"

"I am the best man," he said with a nod.

She nodded, letting the conversation come to a close. Jess walked down the stairs and stopped at his beat up Voltswagen. He looked over his shoulder, throwing her a tight smile and a small wave before opening the door. He climbed inside without looking back a second time. Rory heard the front door open and her grandparents came to stand on either side of her as she watched his car drive away.

"It was a lovely dinner Rory. Thank you for letting me take the rest of the pie home and tell Sookie thank you for making it for me," Richard said politely.

"You're welcome Grandpa and I'll pass along the message."

The door opened once more and Lorelai came out holding Rory's phone out to her.

"It's Dean," she explained.

"Go ahead and take it Rory. We're leaving anyway," Emily said with a pleasant smile.

She hugged them both before taking her phone from her mom. She waited until she was inside before putting it to her ear.

"Dean?"

"I'm here. Happy Thanksgiving."

"You too," she said with a smile in her voice.

"Your house sounds as packed as my aunt's."

"They're starting to leave now. My grandparents are saying goodbye to my mom and Jess left ten minutes ago."

"Jess was there? I thought your grandmother hated him."

"She was the epitome of grace amd they got along but I can't say the same for Jess' mom. I think she might have scared my grandmother into shock if today hadn't been so important to me."

"I've heard from people that she's ecentric," he said with a laugh.

"Oh she's more than ecentric. Lets just say that I sympathize with Jess. He couldn't have had an easy childhood."

"Do you think that we could do something when I get back on Sunday?"

"What did you have in mind?"

"We could go out for coffee or get some dinner."

"Are you asking me out on a date?" she teased.

"It's just coffee or dinner. I figured I'd support your habit," he laid with a throaty laugh.

"Dinner sounds great," she agreed.

"I know of this really great Greek place in Hartford that I think you'll like."

"I've never food before."

"I figured you hadn't but I know that you aren't scared of trying anything once."

"I'll see you Sunday."

The conversation wound down and she waved to Liz and TJ before they walked out the door. Lorelai and Luke were in the kitchen having a cup of coffee for her and a beer for him. Lorelai heard Rory's end of the conversation and hoped that things worked out for Rory and Dean. Rory deserved to have a chance at something good and Lorelai had a feeling that Dean was the guy to make that happen. He may have let her down before but he was older and wiser and he had a record of treating Rory with respect and he generally cared for her. That was the kind of guy she needed.


End file.
